A park with a statue of a figure on horseback, surrounded by leafless trees and a clear sky.

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Windsor vacation rentals

Property grounds

1. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
$682 nightly
The price is $769
Sep 9 - Sep 10
Total with taxes and fees
Wildflower
Dining

2. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very Good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
$1,155 nightly
The price is $1,297
Aug 16 - Aug 17
Total with taxes and fees
Elegant Vineyard Living at a Private Wine Country Estate
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, WiFi (free), bed sheets

3. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (126 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
$123 nightly
The price is $140
Aug 19 - Aug 20
Total with taxes and fees
Wildhaven Sonoma Glamping
Exterior

4. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.6 out of 10, Exceptional, (5 reviews)
"Nice camping spot "
United States
Evelyn
$67 nightly
The price is $77
Aug 12 - Aug 13
Total with taxes and fees
The Ranch at Lake Sonoma
Coffee/tea maker, fridge, microwave, oven

5. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
$366 nightly
The price is $411
Aug 12 - Aug 13
Total with taxes and fees
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

6. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
$332 nightly
The price is $373
Aug 19 - Aug 20
Total with taxes and fees
Wine Country Cottage Escape
Terrace/patio

7. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (35 reviews)
"Great stay, highly recommend!"
United States
Jana P.
$433 nightly
The price is $479
Aug 31 - Sep 1
Total with taxes and fees
Somms Rest ⎮ Designed. Curated. Peaceful.
Outdoor pool

8. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
$228 nightly
The price is $256
Aug 23 - Aug 24
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
Smart TV

9. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
$481 nightly
The price is $533
Aug 31 - Sep 1
Total with taxes and fees
Serenity at the Russian River
Interior

10. 2BR Bungalow - Russian River & Wine Country

2BR Bungalow - Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (17 reviews)
"Had a great stay. Great host and location. Very quiet and relaxing. "
United States
Robert A.
$396 nightly
The price is $447
Aug 16 - Aug 17
Total with taxes and fees
2BR Bungalow - Russian River & Wine Country
Dining

11. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (12 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
$400 nightly
The price is $442
Aug 19 - Aug 20
Total with taxes and fees
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Property grounds

12. Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (51 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
$445 nightly
The price is $491
Aug 16 - Aug 17
Total with taxes and fees
Private Lofted Downtown Studio
Dining

13. Wine Country Getaway

Wine Country Getaway
Mirabel Heights
10.0 out of 10, Exceptional, (33 reviews)
"Everything was perfect and people in change of the hotel were incredible "
United States
dalton s.
$512 nightly
The price is $566
Aug 25 - Aug 26
Total with taxes and fees
Wine Country Getaway
Beach

14. The Tiny Tipsy Turtle

The Tiny Tipsy Turtle
Guerneville
10.0 out of 10, Exceptional, (62 reviews)
"Great little place to stay / perfect location in town close to everything / wonderful front patio "
United States
ANTHONY B.
$203 nightly
The price is $217
Sep 1 - Sep 2
Total with taxes and fees
The Tiny Tipsy Turtle
Dining

15. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (84 reviews)
"Awesome pet friendly home with nice backyard, great location. Really enjoyed our two night stay in this well appointed home while visiting surrounding areas. Cynthia responded so quickly to any of our questions. Would love to stay here again! "
United States
Keri S.
$715 nightly
The price is $803
Aug 14 - Aug 15
Total with taxes and fees
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Outdoor dining

16. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
$525 nightly
The price is $589
Aug 16 - Aug 17
Total with taxes and fees
Russian River Brew-cation Home
Outdoor dining

17. Peaceful, charming, cottage in wine country. Beautiful yard!

Peaceful, charming, cottage in wine country. Beautiful yard!
Sebastopol
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful, charming cottage in a quiet neighborhood. Close to wineries and food."
United States
Mikaela
$324 nightly
The price is $358
Aug 12 - Aug 13
Total with taxes and fees
Peaceful, charming, cottage in wine country. Beautiful yard!
TV, fireplace

18. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (74 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
$543 nightly
The price is $610
Aug 17 - Aug 18
Total with taxes and fees
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Game room

19. Relaxing Vineyard View, Rooftop Deck & Game Room

Relaxing Vineyard View, Rooftop Deck & Game Room
Sebastopol
10.0 out of 10, Exceptional, (24 reviews)
"The location was perfect if you enjoy the Russian River Wineries and the Healdsburg area. The house itself is full of charm and character. It was nice to be able to unwind with friends at the dining table and play cards after a collaboratively cooked meal. The little town of Graton has a couple of good little restaurants, too!"
United States
Jeff D.
$468 nightly
The price is $525
Aug 12 - Aug 13
Total with taxes and fees
Relaxing Vineyard View, Rooftop Deck & Game Room
Exterior

20. Sebastopol Lux Walk toTown Guest Suite

Sebastopol Lux Walk toTown Guest Suite
Sebastopol
9.0 out of 10, Wonderful, (6 reviews)
"Beautiful place. Bed was extremely comfortable. Overall environment was pleasant. Coffee set up was good for me as a black coffee drinker. We would stay again and would happily recommend it to others."
United States
Brad
$262 nightly
The price is $281
Sep 9 - Sep 10
Total with taxes and fees
Sebastopol Lux Walk toTown Guest Suite
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor Hotel Reviews

Hotel La Rose

Hotel La Rose

10/10 Excellent
"This place is great! Great location, hotel is really nice and staff are very helpful and do a great job."
Joe 2-night trip
Posted 1 hour ago
Hotel La Rose

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $77 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Windsor?

Yes, we have vacation rentals in Windsor near Dom Whitney Tasting Lounge, or you can go with a secluded option if you're looking for a relaxing stay. Our travelers say Windsor has a good selection of top-notch restaurants and wineries. Make sure you have time to check out the festivals while you're in the area.

What's the top vacation rental that Windsor has to offer?

Bodega Bay - Sonoma Coastline: Visitors like this Windsor vacation home rental. It is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals are there in Windsor?

Choose from 31 Expedia vacation rentals in Windsor for a memorable vacation.

What can I see and do in Windsor?

Family-friendly attractions include Dom Whitney Tasting Lounge and Powell's Sweet Shoppe - Windsor, whereas Russian River is a spot to enjoy the outdoors. Windsor Golf Club and Pacific Coast Air Museum are other places to visit while you're in town.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Windsor. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a small group gathering.